3-Methoxy-4',5-dihydroxy-trans-stilbene

Base Information

• Chemical Name: 3-Methoxy-4',5-dihydroxy-trans-stilbene
• CAS No.: 42438-89-1
• Molecular Formula: C15H14 O3
• Molecular Weight: 242.274
• Hs Code.: 2909500000
• European Community (EC) Number: 694-822-2
• NSC Number: 723532
• UNII: 4PAK325BEM
• DSSTox Substance ID: DTXSID50420234
• Nikkaji Number: J1.960.641D,J2.480.575A
• Wikipedia: Pinostilbene
• Wikidata: Q18388690
• Pharos Ligand ID: 398QWN36K5GK
• Metabolomics Workbench ID: 62887
• ChEMBL ID: CHEMBL498917
• Mol file: 42438-89-1.mol

Synonyms:3,4'-dihydroxy-5-methoxystilbene;pinostilbene

Chemical Property of 3-Methoxy-4',5-dihydroxy-trans-stilbene

Chemical Property:

• Vapor Pressure: 7.17E-09mmHg at 25°C
• Melting Point: 117-118℃
• Boiling Point: 454.3oC at 760 mmHg
• Flash Point: 228.5oC
• PSA: 49.69000
• Density: 1.252g/cm3
• LogP: 3.27680
• Storage Temp.: 2-8°C
• Solubility.: DMSO: ≥13mg/mL
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 242.094294304
• Heavy Atom Count: 18
• Complexity: 269

Purity/Quality:

98%,99%, ^*data from raw suppliers

Pinostilbene ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi,N
• Statements: 37/38-41-50
• Safety Statements: 26-39-61

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC(=CC(=C1)O)C=CC2=CC=C(C=C2)O
• Isomeric SMILES: COC1=CC(=CC(=C1)O)/C=C/C2=CC=C(C=C2)O

Technology Process of 3-Methoxy-4',5-dihydroxy-trans-stilbene

There total 14 articles about 3-Methoxy-4',5-dihydroxy-trans-stilbene which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

3,5,4'-trimethoxy-trans-stilbene (22255-22-7) → pinostilbene (42438-89-1)

Guidance literature:

With lithium thioethoxide; In N,N-dimethyl-formamide; at 160 ℃; for 2h;

DOI:10.1070/mc2002v012n05abeh001616

Reference yield: 92.0%

1-Benzyloxy-3-[(E)-2-(4-benzyloxy-phenyl)-vinyl]-5-methoxy-benzene (68692-55-7) → pinostilbene (42438-89-1)

Guidance literature:

With hydrogen; In dichloromethane; at 20 ℃; for 5h; under 3750.38 Torr;

Reference yield: 9.5%

(E)-5-[2-4-(hydroxyphenyl)ethenyl]-1,3-benzenediol (501-36-0) + methyl iodide (74-88-4) → pinostilbene (42438-89-1) + 3,5,4'-trimethoxy-trans-stilbene (22255-22-7) + 5-[(E)-2-(4-methoxyphenyl)vinyl]benzene-1,3-diol (65728-21-4,33626-08-3) + 3,5-dimethoxy-4'-hydroxy-trans-stilbene (537-42-8,18259-15-9) + 3,4'-dimethoxy-5-hydroxystilbene (58436-29-6)

Guidance literature:

(E)-5-[2-4-(hydroxyphenyl)ethenyl]-1,3-benzenediol; With sodium hydride; In N,N-dimethyl-formamide; at -5 - 0 ℃; for 0.5h; Inert atmosphere;

methyl iodide; In N,N-dimethyl-formamide; at -5 - 20 ℃; for 18h; Inert atmosphere;

DOI:10.1021/np5002576

upstream raw materials:

3,5,4'-trimethoxy-trans-stilbene

2-(3,5-dimethoxyphenyl)-1-(4'-methyoxyphenyl)ethan-1-ol

3,5-dimethoxy-4'-hydroxy-trans-stilbene

(E)-5-[2-4-(hydroxyphenyl)ethenyl]-1,3-benzenediol

Downstream raw materials:

3,4'-dihydroxy-5-methoxybibenzyl

C₁₅H₁₄O₆S

(E)-4-(3-hydroxy-5-methoxystyryl)phenyl 2-acetoxybenzoate

3,4'-dihydroxy-5-methoxy-trans-stilbene 4'-O-β-D-glucopyranoside

Refernces

• 1、 -. "Method for synthesizing artificially all-trans-resveratrol and derivative thereof". Paragraph 0069; 0070. . Retrieved 2017/08/31.
• 2、 Houillé, Benjamin,Papon, Nicolas,Boudesocque, Leslie,Bourdeaud, Eric,Besseau, Sébastien,Courdavault, Vincent,Enguehard-Gueiffier, Cécile,Delanoue, Guillaume,Guérin, Laurence,Bouchara, Jean-Philippe,Clastre, Marc,Giglioli-Guivarc'H, Nathalie,Guillard, Jér?me,Lanoue, Arnaud. "Antifungal activity of resveratrol derivatives against Candida Species". . p. 1658 - 1662. Retrieved 2014/08/18.